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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-02-04 10:21:51 UTC
Update Date2019-07-23 05:56:16 UTC
HMDB IDHMDB0011678
Secondary Accession Numbers
  • HMDB11678
Metabolite Identification
Common NameGeranylgeranylcysteine
DescriptionGeranylgeranylcysteine is a modified thioether amino acid in which an isoprenyl group (geranylgeranyl) has been attached to the sulfhydryl group of cysteine through a thioether bond. Geranylgeranylcysteine is typically formed through posttranslational (prenylation) protein modification whereupon degradation of the parent protein leaves the modified (prenylated) amino acid. Prenylation is a relatively recently discovered post-translational modification of proteins that directs cytosollic proteins to membranes while at the same time activating them functionally. The change in hydrophobicity that is essential for membrane binding is done via the covalent attachment of a polyisoprene (such as a farnesyl or geranylgeranyl group) to a C-terminal cysteine by a thioether bond. Prenylated proteins can comprise up to 2% of total cellular protein. Prenylcysteine lyase is an enzyme that is capable of cleaving the thiother bond in prenylcysteines and is used to help in the turnover of prenylated proteins. Prenylcysteine lyase deficiency leads to the accumulation of farnesylcysteine and geranylgeranylcysteine in brain and liver. (PMID: 9287348 ).
Structure
Data?1563861376
Synonyms
ValueSource
S-(3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraenyl)-(e,e,e)-L-cysteineHMDB
S-[(2E,6E,10E)-3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraenyl]- (9ci)-L-cysteineHMDB
Chemical FormulaC23H37NO3S
Average Molecular Weight407.61
Monoisotopic Molecular Weight407.249414745
IUPAC Name(2R)-3-sulfanyl-2-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenamido]propanoic acid
Traditional Name(2R)-3-sulfanyl-2-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenamido]propanoic acid
CAS Registry Number169523-06-2
SMILES
SC[C@H](NC(=O)\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=O
InChI Identifier
InChI=1S/C23H37NO3S/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-22(25)24-21(16-28)23(26)27/h9,11,13,15,21,28H,6-8,10,12,14,16H2,1-5H3,(H,24,25)(H,26,27)/b18-11+,19-13+,20-15+/t21-/m0/s1
InChI KeyUBCKUGRWFMEXIF-WONWMLGISA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentAcyclic diterpenoids
Alternative Parents
Substituents
  • Acyclic diterpenoid
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • Cysteine or derivatives
  • Alpha-amino acid or derivatives
  • N-acyl-amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Alkylthiol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0017 g/LALOGPS
logP5.58ALOGPS
logP5.65ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)4.04ChemAxon
pKa (Strongest Basic)1.45ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity123.68 m³·mol⁻¹ChemAxon
Polarizability48.79 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-8889000000-3f81e03325547663218eJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-022l-9352500000-a735063f6d3013ad3130JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-2769600000-ec3a2eaceb3ae67eb426JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ads-4961000000-44253e7d991961cef89dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ar0-8950000000-13cfd8c2ae6c7a125a61JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ab9-2017900000-84ecb7d4aa334cb77ecfJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-059i-4329200000-97099be07e7e001431c7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-008l-9350000000-4a227b58aca7450e328bJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028366
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481025
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Zhang L, Tschantz WR, Casey PJ: Isolation and characterization of a prenylcysteine lyase from bovine brain. J Biol Chem. 1997 Sep 12;272(37):23354-9. [PubMed:9287348 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.